Tetrahydrofuran → {[7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}carbamic azide

HRID 711404Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17]C(O)=O)[N:11]3[CH:21]=2)[CH:5]=[CH:6][CH:7]=1.[N-:22]=[N+:23]=[N-:24].[Na+].C1C=CC(P([N:40]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C1[CH2:47][O:46]CC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[O:16])[NH:14][CH2:13][CH:12]([CH2:17][NH:40][C:47]([N:22]=[N+:23]=[N-:24])=[O:46])[N:11]3[CH:21]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 33557Sodium Azide

HCID 199401P,P-Diphenylphosphinic azide

HCID 56766546[7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetic acid

Product 1

HCID 86732553{[7-(3-Chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}carbamic azide

Procedure

100 mg (0.328 mmol) of [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetic acid and NaN3 (664 mg, 0.98 mmol) were suspended in 10 ml of dry THF, 108 mg of DPPA (0.394 mmol) was added. The mixture was stirred at room temperature for 18 h. The volatiles were removed under vacuo and the residue was purified by flash chromatography (DCM/EtOAc/EtOH 6/3/1) to give the desired compound and a secondary compound.

Workup

customThe volatiles were removed under vacuo
customthe residue was purified by flash chromatography (DCM/EtOAc/EtOH 6/3/1)

Sources & evidence

ORD record: ord-af6b37648428426d9d473f99bfa879ec
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181258B2

Reaction notes

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